Ammonium Chloride → 2-(3-methoxypyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole

HRID 1256596Notes

Reaction equation

HRID 1256596 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:12]([CH3:13])[C:11]2[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:20])[F:19])=[CH:17][C:10]=2[N:9]=1.[CH3:22][O-:23].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:22][O:23][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:12]([CH3:13])[C:11]2[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:20])[F:19])=[CH:17][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 666115222-(3-fluoropyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole

Product 1

HCID 666121812-(3-methoxypyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazoleYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.30 g of 2-(3-fluoropyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole and 10 ml of DMF was added 0.16 g of sodium methoxide under ice cool, then, the mixture was heated up to room temperature and stirred for 1.5 hours. A saturated ammonium chloride aqueous solution was poured, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.28 g of 2-(3-methoxypyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter, referred to as present active compound 8).

Workup

  1. temperaturecool
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf39f03d876142a2986eef2d5debb160
Source dataset
uspto-grants-2013_06
Patent number
US08461181B2

Reaction notes

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